Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

Abstract

The palladium-catalyzed synthesis of indole/benzofuran-containing diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η³-C₃H₅)Cl]₂/XPhos while with benzofuranylmethyl acetates Pd₂(dba)₃/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

Key words

palladium - boronic acids - Suzuki–Miyaura reaction - indoles - benzofurans - diarylmethanes

Publication History

Received: 15 August 2021

Accepted after revision: 07 October 2021

Article published online:
11 November 2021

• References

• 1a Hendrich CM, Bongartz LM, Hoffmann MT, Zschieschang U, Borchert JW, Sauter D, Krämer P, Rominger F, Mulks FF, Rudolph M, Dreuw A, Klauk H, Hashmi AS. K. Adv. Synth. Catal. 2021; 363: 549
• 1b Jiao C, Huang KW, Luo J, Zhang K, Chi C, Wu J. Org. Lett. 2009; 11: 4508
• 1c Jung I, Lee JK, Song KH, Song K, Kang SO, Ko J. J. Org. Chem. 2007; 72: 3652
• 1d Hwu JR, Chuang KS, Chuang SH, Tsay SC. Org. Lett. 2005; 7: 1545
• 2a Heravi MM, Zadsirjan V. RSC Adv. 2020; 10: 44247
• 2b Miao Y.-h, Hu Y.-h, Yang J, Liu T, Sun J, Wang X.-j. RSC Adv. 2019; 9: 27510
• 2c Heravi MV, Zadsirjan V, Hamidi H, Amiri PH. T. RSC Adv. 2017; 7: 24470
• 2d Hiremathad A, Patil MR, Chethana KR, Chand K, Santos MA, Keri RS. RSC Adv. 2015; 5: 96809
• 3 Chauhan M, Saxena A, Saha B. Eur. J. Med. Chem. 2021; 218: 113400
• 4a Dorababu A. RSC Med. Chem. 2020; 11: 1335
• 4b Wang W.-J, Wang L, Liu Z, Jiang R.-W, Liu ZW, Li M.-M, Zhang Q.-W, Dai Y, Li Y.-L, Zhang X.-Q, Ye W.-C. Phytochemistry 2016; 122: 238
• 4c He S, Jain P, Lin B, Ferrer M, Hu Z, Southall N, Hu X, Zheng W, Neuenswander B, Cho C.-H, Chen Y, Worlikar SA, Aubé J, Larock RC, Schoenen FJ, Marugan JJ, Liang TJ, Frankowski KJ. ACS Comb. Sci. 2015; 17: 641
• 5 Sharma S, Kumar D, Singh G, Monga V, Kumar B. Eur. J. Med. Chem. 2020; 200: 112438
• 6a Han Y, Dong W, Guo Q, Li X, Huang L. Eur. J. Med. Chem. 2020; 203: 112506
• 6b Jia Y, Wen X, Gong Y, Wang X. Eur. J. Med. Chem. 2020; 200: 112359
• 7a Dadashpoura S, Emami S. Eur. J. Med. Chem. 2018; 150: 9
• 7b Singh TP, Singh OM. Mini-Rev. Med. Chem. 2018; 18: 9
• 7c Chadha N, Silakari O. Eur. J. Med. Chem. 2017; 134: 159
• 7d Sravanthi TV, Manju SL. Eur. J. Pharm. Sci. 2016; 91: 1
• 7e Gribble GW. Indole Ring Synthesis: From Natural Products to Drug Discovery. Wiley; Weinheim: 2016
• 7f Zhang MZ, Chen Q, Yang GF. Eur. J. Med. Chem. 2015; 89: 421
• 7g Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
• 7h Croxtall JD, Plosker GL. Drugs 2009; 69: 339
• 7i Clemett D, Spencer CM. Drugs 2000; 60: 379

For biological activity of benzylated indoles, see:
• 8a Karg E.-M, Luderer S, Pergola C, Bühring U, Rossi A, Northoff H, Sautebin L, Troschütz R, Werz O. J. Med. Chem. 2009; 52: 3474
• 8b Bhurruth-Alcor Y, Rost T, Jorgensen MR, Kontogiorgis C, Skorve J, Cooper RG, Sheridan JM, Hamilton WD. O, Heal JR, Berge RK, Miller AD. Org. Biomol. Chem. 2011; 9: 1169
• 8c Righi M, Topi F, Bartolucci S, Bedini A, Piersanti G, Spadoni G. J. Org. Chem. 2012; 77: 6351
• 9 Dongyin C, Lili F, Fe L, Lei Y, Gang S, Xua C, Feng H. CN111675644, 2020
• 10a Ila H, Markiewicz JT, Malakhov V, Knochel P. Synthesis 2013; 2343
• 10b Kearney JA. M, Landry-Bayle A, Gomez L. Tetrahedron Lett. 2010; 51: 2281
• 10c Iwanowicz EJ, Lau WF, Lin J, Roberts DG. M, Seiler SM. Bioorg. Med. Chem. Lett. 1996; 6: 1339
• 10d Labadie SS, Teng E. J. Org. Chem. 1994; 59: 4250
• 10e Matassa VG, Maduskuie TP, Shapiro HS. Jr, Hesp B, Snyder DW, Aharony D, Krell RD, Keith RA. J. Med. Chem. 1990; 33: 1781
• 11a Kuriyama M, Shinozawa M, Hamaguchi N, Matsuo S, Onomura O. J. Org. Chem. 2014; 79: 5921
• 11b Schmink JR, Tudge MT. Tetrahedron Lett. 2013; 54: 15
• 12a Schade MA, Metzger A, Hug S, Knochel P. Chem. Commun. 2008; 3046
• 12b Manolikakes G, Hernandez CM, Schade MA, Metzger A, Knochel P. J. Org. Chem. 2008; 73: 8422
• 13a Konishi H, Itoh T, Manabe K. Chem. Pharm. Bull. 2010; 58: 1255
• 13b Yamaguchi M, Manabe K. Org. Biomol. Chem. 2017; 15: 6645
• 14a Tangdenpaisal K, Phakhodee W, Ruchirawat S, Ploypradith P. Tetrahedron 2013; 69: 933
• 14b Mendoza O, Rossey G, Ghosez L. Tetrahedron Lett. 2011; 52: 2235
• 14c Mendoza O, Rossey G, Ghosez L. Tetrahedron Lett. 2010; 51: 2571
• 14d Primault G, Legros J.-Y, Fiaud J.-C. J. Organomet. Chem. 2003; 687: 353
• 15 Yang L, Chen X, Ni K, Li Y, Wu J, Chen W, Ji Y, Feng L, Li F, Chen D. Tetrahedron Lett. 2020; 61: 152123 ; and references therein
• 16 Arcadi A, Fabrizi G, Fochetti A, Ghirga F, Goggiamani A, Iazzetti A, Marrone F, Mazzoccanti G, Serraiocco A. RSC Adv. 2021; 11: 909
• 17 Stewart GW, Maligres PE, Baxter CA, Junker EM, Krska SW, Scott JP. Tetrahedron 2016; 72: 3701
• 18a Najib A, Hirano K, Miura M. Org. Lett. 2017; 19: 2438
• 18b Makida Y, Usui K, Ueno S, Kuwano R. Chem. Lett. 2017; 46: 1814
• 18c Le Bras J, Muzart J. Eur. J. Org. Chem. 2016; 2565
• 18d Kuwano R. Synthesis 2009; 1049
• 18e Liégault B, Renaud J.-L, Bruneau C. Chem. Soc. Rev. 2008; 37: 290
• 18f Kuwano R, Kusano H. Org. Lett. 2008; 10: 1979
• 18g Kuwano R, Kusano H. Chem. Lett. 2007; 36: 528
• 18h Yokogi M, Kuwano R. Tetrahedron Lett. 2007; 48: 6109
• 18i Johns AM, Tye JW, Hartwig JF. J. Am. Chem. Soc. 2006; 128: 16010
• 18j Kuwano R, Kondo Y. Org. Lett. 2004; 6: 3545
• 18k Kuwano R, Kondo Y, Shirahama T. Org. Lett. 2005; 7: 2973
• 18l Kuwano R, Kondo Y, Matsuyama Y. J. Am. Chem. Soc. 2003; 125: 12104
• 19a McGarry KR, McDaniel M, Chan BC, O’Connor AR. Polyhedron 2016; 114: 101
• 19b DeAngelis AJ, Gildner PG, Chow R, Colacot TJ. J. Org. Chem. 2015; 80: 6794
• 20 Govek SP, Overman LE. J. Am. Chem. Soc. 2001; 123: 9468
• 21 Ambrogio I, Cacchi S, Fabrizi G, Prastaro A. Tetrahedron 2009; 65: 8916
• 22 Wang D, Chen Q, Li W, Yu C, Zhou Y, Zhang X. J. Am. Chem. Soc. 2010; 132: 8909
• 23 Lafzi F, Kilic H, Saracoglu N. J. Org. Chem. 2019; 84: 12120
• 24 Biswas J. Tetrahedron 1969; 25: 227
• 25 Hikawa H, Kotaki F, Kikkawa S, Azumaya I. J. Org. Chem. 2019; 84: 1972
• 26 Tang Y, Zhuang K, Zhang X, Xie F, Yang L, Lin B, Cheng M, Li D, Liu Y. Eur. J. Org. Chem. 2020; 3441
• 27 Chu X, Jiang R, Fang Y, Gu Z, Meng H, Wang S, Ji S. Tetrahedron 2013; 69: 1166
• 28 Huang C, Kuo C, Kavala V, Yao C. Eur. J. Org. Chem. 2016; 2720
• 29 Nishiyama T, Hatae N, Yoshimura T, Takaki S, Abe T, Ishikura M, Hibino S, Choshi T. Eur. J. Med. Chem. 2016; 121: 561
• 30 Udagawa T, Kogawa M, Tsuchi Y, Watanabe H, Yamamoto M, Kawatsura M. Tetrahedron Lett. 2017; 58: 227
• 31 Cervantes-Reyes A, Rominger F, Hashmi AS. K. Chem. Eur. J. 2020; 5530
• 32 Duez S, Steib AK, Knochel P. Org. Lett. 2012; 14: 1951
• 33 Yu H, Zhang M, Li Y. J. Org. Chem. 2013; 78: 8898